反应详情

2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196°-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1H), 8.36 (dd, J=8.1, 0.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.28-7.45 (m, 4H), 7.16-7.26 (m, 4H), 7.00-7.08 (m, 2H), 6.24 (d, J=1.8 Hz, 1H), 3.97 (s, 2H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34.

1. temperaturethe mixture was heated
2. temperatureto reflux under a Dean-Stark trap
3. concentrationthe reaction was concentrated
4. customthe residue was chromatographed on silica gel (50% EtOAc/CHCl3)